Chance Encounter
by jeromevaleska
Summary: You end up meeting Jerome upon doing business for Oswald and you almost instantly take a liking to each other.
You didn't expect to stumble upon a duplicitous, alluring ginger the night you were out on business for your boss, Oswald Cobblepot, but nothing was what you expected in Gotham, which was what you loved about the city.

It was only supposed to be a simple slash and leave, but the weeping ginger caught your eye. You wondered why Oswald sent you downtown to the circus of all places but then you vaguely remembered him claiming that one of the performers owed him money and wouldn't pay his dues so the man simply had to go.

Oswald never doubted that you would get the job done, which is why he entrusted you to be his second in command. He'd give the order and you followed through with each one, no questions asked. You knew how to lure your victims in with your sweet, seductive charm. You were also one hell of an actress so if you needed to bring out the waterworks to catch someone off guard you could do so on a whim. Which is why you knew the redhead was spewing out crocodile tears because that was your specialty.

You had just finished up with your assignment for the day but you stopped in your tracks when you heard him sobbing. You stood at a distance so no one could see you as you watched. You spotted Jim Gordon with his girlfriend Leslie Thompkins who were investigating the mishap that occurred. It didn't take long for you to figure out that the redhead was mourning the loss of his mother. Though, who was to say it was a loss at all when he killed her himself. He may have fooled them, but he couldn't trick you, no, not with that overly dramatic fall to his knees, it was all too staged. It was obvious that he was just putting on a show in hopes that he wouldn't get caught.

When the others disappeared from view and the area was clear, you decided that you should approach the boy because he piqued your interest. You wanted to know more about him, more about what was underneath the mask he wore so you could dig into all the dark secrets he hid.

"Jerome, is it?" you asked with an innocent tilt of your head, a soft smile playing on your lips. He snapped his head up and turned to look at you.

With a sniff and wipe of his eyes he replied, "Yeah," he paused before asking, "and you are?"'

"I'm Y/N," you introduced yourself with a friendly smile. You extended your arm over so he could shake your hand and he reluctantly took it despite his quivering motions.

"Can I help you with something?" he stammered as he met your eyes.

"I just overheard what happened, and I wanted to give my condolences. I'm really sorry about your mother," you apologized and took a step closer, placing your hand on his shoulder, following his eyes as they strayed away back to the ground.

He took a moment just to breathe, shaking his head in disbelief, and he looked back at you with those puffy bright red eyes before he answered, "I… I need a moment, thank you for being so kind, but I'm still processing," he choked out, and you narrowed your eyes as you examined his every movement to the look on his face, to his fidgety hands, to the way he carried himself, you took it all in.

"Okay cut that shit out," you blurted out, unable to stomach his act for another second.

"I beg your pardon?" he questioned, raising an eyebrow from your sudden change in tone.

"Enough with the boo-hoos and the mama's boy act, I know what you did," you admitted with a chuckle.

But he still kept up with the facade, his eyes watering at the corners as he tried to blink them away, and he murmured softly, "What? What are you on about?"

You cocked an eyebrow at him with a skeptical look on your face and a shake of your head, your piercing eyes remained unwavering.

"You don't have to pretend with me, I'm not going to fink on you," you assured, "I'll even pinky promise you if you need more reassurance," you mimicked his overly soft and boyish voice while you reached out your pinky finger to him.

Then in a second, his whole demeanor changed.

"I gotta say, I'm impressed, you've got a good eye, gorgeous," he finally admitted. His cheeks were still stained with tears though they didn't match the awakened devilish glint in his eye when he stared back at you. He grinned from ear to ear and his voice didn't sound so shaky and unsure of itself, it was gravelly and biting.

"Damn right I do," you boasted, "I know how to spot the crocodile tears the second I see them, because well, I practically invented it," you added with a soft laugh. His eyes grew dark and dangerous, his smirk amused and interested. "That's the guy I was looking for," you chortled as you pointed your finger in his direction.

"Ha! You're all talk and no show," he dared, and you just laughed in response.

"Well maybe you'll learn more about me if you can avoid getting caught, which I highly doubt," you taunted, and he made a snorting sound at your sassy comment. "Even if they don't suspect anything now, they will, soon enough," you told him and he looked entertained, his eyebrows furrowed as he listened. "First time?" you asked.

"As far as I'm concerned, that's none of your business, gorgeous," he replied with a dark, quiet chuckle.

"You don't need to answer, I can tell," you quipped, "you'll learn," you continued to tease.

"Aw, aren't you cute?" he said mockingly, his eyes looking you up and down, taking the sight of you and his grin only widening as you smiled back. "I'd love to stay and chat,, but I'd best take my leave, any minute now the po-po will haul all our asses down at the precinct," he mumbled the last part under his breath.

"That's a shame, but I will leave you to it," you said with a shrug of your shoulders.

"But I will definitely be seeing you around gorgeous," he cooed and winked at you flirtatiously before you started walking away.

"Give them hell," you told him, turning around to wink back at him. He sauntered back to his trailer and you found yourself observing him as he did the same, you both exchanged knowing looks until the moment he shut the door to it.

It wasn't long after that day that you found out he was hauled off to Arkham Asylum. You were not surprised to hear those news in the slightest. While he was away, you couldn't help but long to see him again. You liked his spirit and his devilish charm, he certainly captured your attention in the short encounter. You had never met another criminal like him, he brought so much more excitement than your boss, Oswald, who was always bickering to you about something he needed done.

You knew the ginger was a cunning one though, so you figured that he would get out of that place eventually, and in his absence you remembered that wickedly gorgeous grin he always wore.

Many days passed until big, exciting news came your way; the breakout at Arkham. It was all over the news, six inmates had broken out, and you couldn't contain your elation upon hearing that was one of the inmates were none other than Jerome Valeska.

Chaos followed him wherever he went and every time his face showed up on the TV screen, you would just watch in amusement. He wanted everyone to know of his crimes, usually the criminals in Gotham didn't like to make a show of their wrongdoings but this one just couldn't get enough of the spotlight on him.

One day, you were at the club, serving drinks to a couple of patrons seated at the tables, it was a regular boring day, and you hadn't expected anything more than the usual activities Oswald had scheduled for you so you were pleasantly surprised when you saw a particular ginger make his way through the door.

You ambled your way over to him with a simper on your face, "How may I help you?" you asked as you tried to stifle the giggle that threatened to fall from your lips. He was grinning like a Cheshire cat while he eyed his surroundings, examining the features of the club before he looked back at you.

"Yeah, would you mind showing me where the back room is?" he answered with a dark chuckle, much to your amusement.

"This way, sir," you set your tray of wine cups down on a table and he held his hand out for you to grab before you led him to one of the private rooms in the back of the club.

"So you work for Oswald, eh? Little shit's lucky," he said, almost in a hiss.

"Yeah, he's got money, something that you probably don't have," you sassed, adding with a soft laugh. "What brings you here, anyway?" you titled your head to the side, your eyebrows raised in question.

"I figured you must have missed me, when we first met you kept batting your eyelashes at me like some kind of lost kitten," he taunted with a roared laugh, "you're even cuter in that tight black dress," he took a long moment to leer you up and down, and you teased him by swaying your hips a little.

"I didn't miss you by the way, I was glad when you got caught," you continued to poke fun at him, "like I knew you would."

"Well all that's history now, doll," his lips curled into a dangerous smirk before he added, "because now I can do whatever the fuck I want when I want."

"You sound like a spoiled brat," you goaded, and you were going to say more but he cut you off by leaning his mouth against your ear, his fingers trailing down the path of your neck.

"Hm, let me repeat that," he said, his voice was raspy, his warm breath hitting your skin in a rush and making you shiver, making you stop entirely as you found yourself arching into his touch. "I said, I can do whatever the fuck," he clutched your wrist suddenly in his hand as he grinned at you, holding it up as he looked back at you with a long smirk. He paused before he added, "I want, when I want."

You were both facing each other, breathing heavily as your eyes wandered down his body then back up. "Oh really huh?" you challenged, "well, I'm waiting," you teased.

He grasped you by your hip, pulling you onto the desk that was in the room, your back facing him in one swift, sudden motion. You giggled as his resolve broke, your game of teasing suddenly over. Your laughter turned to a gasp when he rolled his hips against the back of your own, making his desire for you known. Keeping one hand anchored at your side, he pressed the other to the desk for leverage.

"This is Oswald's desk, you know," you uttered with another laugh, much to his mirth, grinning widely at that.

"Oh, this is Penguin's desk?" he seemed even more aroused knowing that bit of information, and he tossed everything that was on it to the ground. "You don't think he'd mind if I fucked you here, right?" he whispered, lips brushing against your ear before he tugged it into his mouth.

"Of course he would," you giggled, "But I always wanted to be fucked on my boss's desk."

You couldn't help the moan that escaped your lips as you ground your ass against his groin, sending hot burning desire through him.

"You're a little minx, ain't ya, doll?" he teased, "And what would he do if he found us, together, like this?" he asked, planting hot, open-mouthed kisses along the column of your throat, his thumb stroking your skin as he held your neck still with one large hand.

"I'd be well and truly fucked," you gasped as he rutted his covered member against you.

He chuckled, "One can only hope."

You smoothed your hands down the side of your skirt, fingers brushing against his as you did so. Slowly, you lifted the slippery fabric, wiggling your rear enticingly against his groin. Up, up up, revealing the lace tops of your stockings, held in place by a garter belt, higher still, until your pert, round ass was bare to him, framed perfectly between stockings, garter, and a lace thong. He groaned as he caressed your skin, relishing the shudder that tore through you at his slow, gentle touches. You purred, bending over the desk enough to display your clothed sex.

"Do you always dress like such a slut for Penguin? Fuck," he swore, his hands trailing little circles over your skin as his member throbbed at the sight of you.

"Maybe this is just the way I like to dress, it's not for either one of you," you replied snarkily.

"Hm, well, either way I'm not complaining," his eyes continued to roam over you, bent and bare for him. He could see the dusky pink of your sweet folds through a screen of black lace and all he wanted to do was touch and kiss and lick. He sank to his knees behind you, his big hands gripping your silk encased thighs, nudging them further apart to accommodate him kneeling between them. Leaning forward, he pressed soft kisses to the dimple at the base of your spine, his thumb caressing the curve of your ass, just along the edge of your panties. Not wanting to ruin the pretty frame that your garter belt made, he hooked his thumb into the delicate fabric of your thong and tugged it to the side.

He smiled, staring at you with appreciation. You were already flushed and glistening with desire for him. Slowly, he ran a finger up and down your slit, spreading your wetness in his wake.

"You have such a pretty cunt," he murmured, planting a soft teasing kiss against you.

You moaned in reply, your hips rolling against his touch in a desperate attempt to build more friction. He continued to grin to himself, he loved seeing you like this, bare and begging, just for him.

He moved back and kissed up your thigh, until his mouth hovered over your sex. Reaching his free hand up, he pressed firmly on your lower back, pushing down and exposing more of you to him.

With broad, flat strokes of his tongue, he began to taste you. He moved slowly, savoring the frustrated little whine that escaped your mouth each time he reached the top of your slit and then followed his path back without touching your pink bud. He peppered light kisses against your folds, flicking his tongue against your sweet skin, nipping here and there. You moaned in response and ground your hips against his face, begging for a firmer touch. He chuckled at your impatience before he pushed his tongue inside of you, savoring the warmth that his member would soon be buried in. He sucked hard, your sweet desire flooding against his tongue. Just when he thought you were about to go mad from his teasing, he dragged his mouth along your seam, and fastened his lips around your clit.

The muffled cry from above him made his member throb, hardening with insistence. He needed to be inside of you, and soon, but first, he wanted to make you come.

He flicked his tongue over your bud while he firmly pressed two fingers inside of you, crooking them against your walls. Already so close to your edge, he felt you clench and ripple at his intrusion. He began pumping in time with the pattern his tongue lavished on your clit.

He could feel you growing wetter and wetter, hips bucking wildly against his face as you writhed above him. Curling his fingers in and up, searching for that sweet spot deep inside of you; he sucked hard, his teeth scraping over you as your legs began to twitch.

"Jerome," you gasped, and he could hear your nails scraping over the surface of the desk, as your release overwhelmed you.

Your legs clamped down and your hips rolled against his face. He withdrew his fingers, and lapped at your sex as it pulsed and dripped into his mouth, his thumb taking over his lips' work on your clit. He could hear you struggling not to scream from it all.

"I could tell you wouldn't last long," he whispered to himself, chuckling darkly as he watched you

You ignored his comment and after a long moment, your hips began to slow their frenzied jerking and you slumped against the desk, breathing heavily. He slowly extricated himself from between your legs. Standing, he leaned over you, chest flush with your back, propping himself on the desk with one hand.

He could feel the heat and wetness of your sex soaking through the front of his trousers, but he didn't care, actually he loved it. He pressed his desire coated fingers to your lips, and you sucked greedily, your tongue laving over his digits, soft moans rumbling at the back of your throat as you tasted yourself on him. Fire flooded through him at the sight of it, at the sounds you made. He was so hard, all he could think about was the throbbing, aching need between his legs, and the memory of how warm and sweet it was to be buried inside of you.

"Good girl," he murmured, kissing your hair just above your ear.

In response, you rubbed yourself against him impatiently, causing him to groan in delight. Slowly, he withdrew his fingers from your mouth and stood up, pulling you along with him. He held you close, rocking his hips against your pert ass, driving his clothed member between your cheeks in a frustrated attempt to alleviate some of his aching need.

You shivered in his arms, head leaning back against his shoulder. He began to unbutton your dress, needing to feel more of your skin. He stroked your neck, running his fingertips along your collarbones, dipping them in the valley between your breasts. You shivered again, your skin rising in goosebumps at his light touch. He stopped his movement just below your bra, toying with the front clasp. He unhooked it, and your breasts sprang free. He cupped them, warm and heavy in his palms, pushing them up and together, his large hands squeezing at the soft flesh. He found that he loved touching and kissing them, feeling them against his body, watching them bounce while you rode him to oblivion. They fit into his hands perfectly, delicate skin spilling over his fingers as he kneaded them. You moaned softly, reaching up a hand to tug at his hair as he rolled your nipples between his fingers.

"Can you feel what you do to me, doll?" he demanded, driving his hips once more into your ass.

"Mmm, yes," you replied, voice breathy as you wiggled back into his groin.

"Good," he whispered, "because I'm going to fuck you with every last inch, doll," he chuckled, "you're going to fucking love it."

He brought one of his hands away from your breasts to cup your face with a firm grip, thumb trailing over your jaw as he tilted your head back. Eyes alight, he studied you, studied the flush on your cheeks, the swollen state of your lips—done, no doubt, to quiet your cries. There was a wild, hungry look in your bright eyes, a look that made him ache to be inside of you.

"Now, if I'm going to fuck you," he started, "no more biting down, I want to hear every moan," he grin wickedly, "I want all of Gotham to hear you fucking moaning my name, got that?" he said hoarsely, and you nodded in response.

He smiled down at you before crashing his lips over yours in a searing kiss. You kissed him back, your mouth hard, and sharp, and wanting. It sent fire roaring through him, stoking higher with each press of your tongue and nip of your teeth. He quickly slipped his hand between your bodies, and undid his belt and zipper. With your help, he pushed his trousers and boxers down just enough to free his member, it fell between your cheeks, hot and heavy.

"Fuck," he uttered. Your body felt so good, so yielding, against the sensitive skin of his length. Rolling his hips, he twitched against you, and you shuddered helplessly in his arms.

"Hands on the desk, doll," he ordered, breaking the kiss.

With reluctance, you turned away from him and set your hands on the desk. You stood, legs spread and skirt rucked up around your hips, balanced on your splayed fingertips. He grabbed your hip with one hand, fingers curving around the crest of your body. With his other hand, he gripped his shaft and stroked the head of his member down the silken skin of your ass. He yanked you closer, and pressed himself between your thighs. You were so unbearably scalding.

"You want it, don't you?" he said in a raspy tone.

"Yes, yes I want it," you begged softly. You began moving, rotating your hips back and forth, stroking his tip with the seam of your sex, your desire starting to drip down on him, coating him and making him ready to enter you.

"Wrong answer," he teased, laughing as he watched you all needy for him. "What's the correct answer, doll?" he trailed a path of hot kisses down your neck.

"I need it, please," you pleaded under your breath.

"There you go!" he congratulated, "Such a smart girl," he cooed. A mewling cry escaped your lips as the crown of his member hit the sweet bundle of nerves above your entrance. He wanted to make you come from that alone but the ache in his thighs was incessant; he needed to be inside of you, to be sheathed in your tight heat, stretching you, filling you, fucking you.

As you rocked forward, dragging the slick slit of your sex over his pulsing crown, he bent his knees. You tilted your hips back, ready for another teasing, tantalizing glide, and he thrust his hips forward, driving you down onto his member. You cried out in ecstasy, hands scrambling for purchase on the desk at the sudden, throbbing intrusion of his girth.

Your eyes snapped open when you heard a voice outside of the room, your heartbeat thundering in your chest, where you were sure it would explode. You both froze save for the shuddering, aching pulses of your joined sex, and waited. But still, even with someone by the door, Jerome's grin didn't cease.

"Hey, Y/N! Everything alright in there?" Butch's voice called, not yet opening the door but clearly hovering on the other side.

Panic flooded through you, but you tried to steady your breathing. Jerome started rocking his hips against you again which made you have to bite back a moan. You could hear him laughing quietly from behind you and it made you want to punch him for finding this whole situation to be such a joke.

"Everything's fine, Butch! I tripped in these stupid shoes," your voice was high, breathless, but it didn't waver. As you spoke, you slowly wiggled your hips back, pushing yourself further down his member in a slow, teasing rhythm, swallowing your moan.

"Oh okay," he replied, still sounding skeptical. "if you're sure."

"Thank you, Butch!" you called, before letting out a sigh of relief.

"Close call," Jerome said with a laugh, "actually not, no doubt he heard you crying like a little bitch."

"Shut up," you growled under your breath before you seated yourself completely down his throbbing length, the heat of your sex enveloping him. "We have to be quiet," you whispered.

You both waited a heartbeat more. The door was silent and you whimpered, squeezing your walls around him in a silent plea for more.

"Aw, but what's the fun in that?" he asked, a seemingly innocent pout on his face.

"Do you want to come or not?" you spat, and he heaved a dramatic sigh at that. He covered your mouth with his hand. Taking a deep breath, he gripped your hip in earnest, and he dragged himself nearly all the way out of you, the cool air making his desire coated member twitch, before slamming back in.

You moaned, your nails reaching over to dig hard into his hip, hard enough to break the skin.

"Hands on the desk, doll," he whispered into your ear, pulling your clenched fingers from his side and pressing them to the surface before you two. "Don't make me tell you again."

You moaned against his hand as he began to work up a savage pace, his hips and member slamming into you, driving your thighs against the edge of the desk. You knew that he was leaving several bruises, beautiful purples and greens but you didn't care because sex with him was as wild as you thought it'd be. You were gasping and moaning into his hand, your tongue, lips, and teeth writing your cries over his skin.

He wrapped his arm around your waist, holding you close as he fucked you senseless. Member sliding in and out of your liquid heat; you were painfully, gloriously, tight around him, pulling him as he pounded you into the desk. You met each of his thrusts with a hard backwards snap of your hips, rutting against him, the sound of your bodies slapping together filling the air. He could feel sweat bead at his brow and run down his back. His muscles burned, ass clenching with each demanding snap of his hips. Fire spread through his body, tearing through him and making every least nerve scream with desire.

He could feel his release building in the pit of his stomach. He leaned forward, kissing your neck, focusing on the salty sweet taste of your skin instead of the inferno burning in his thighs. He pressed his lips up and down your throat, sometimes bruising hard, sometimes feather light. Higher and higher, until he reached your ear.

"Do you feel me inside of you, doll? Do you feel me splitting you?" he hissed, his breath ghosting over your kiss-slicked skin.

You nodded against his hand, your hips rotating in time to his brutal thrusts. He could feel your heat fluttering around him, your response to his voice immediate and gratifying.

"I fucking love this," he continued, panting as his lips scraped against the corner of your jaw. "Being inside you. Filling you. There is nothing more beautiful than watching my seed drip out of that pretty little cunt of yours."

The sound you made at that, hard and choking at the back of your throat, nearly made him spill right then, but he grit his teeth and continued, his hips rocking against you, his member dragging in and out of the burning embrace of your entrance.

"Well, perhaps the look on your face as you unravel for me, eyes screwed shut and mouth open, calling my name," he closed his eyes, picturing it. "Oh doll, there's nothing sweeter than that."

You were shaking, trembling, in his arms, hot puffs of breath ghosting over his hand, and he knew you wouldn't be able to last much longer. He could feel your sex begin to clamp impossibly tight around him, drawing him in as you tumbled closer to your release. Grabbing the back of your neck, he bent you completely over the desk, opening you wide to his member, as you sagged against the solid surface. His hand still covering your mouth, you came, legs kicking up around him. The sight of you, writhing and desperate, completely and utterly at the mercy of your pleasure sent fire coursing through his veins. Hips frantic in their thrusting, he leaned forward and bit down hard on your shoulder to stifle the snarling growls that rumbled through his chest.

You bucked against him, meeting the final thrust of his hips before you drew him in and didn't let go until he'd spilled every last drop of his release so deep inside of you. The world blazed white, burning away until there was nothing but the warmth of you around him, throbbing and aching together as one.

Breathing heavily, he stumbled backwards enough to pull out of you, his head falling against your shoulder. You laid prone below him, your breath rising in harsh, panting gulps.

"That was…" you paused, your voice still quiet, "wow."

He chuckled, shaking his head. "I'd love to see what else you can do, doll, though sadly we'll have to save it till next time," he looked down at you with that smug grin.

"Next time?" you asked, "What makes you think there will be a next time?" you raised an eyebrow at him and he laughed in response.

"Eh," he shrugged before he continued, "maybe it was the way you listened to whatever I told you or the way your dripping cunt squeezed me or the way you cried my name before that shithead appeared at the door or the way you came after I ate you out," he continued with a laugh, "need I say more?" he asked, his grin never faltering.

"No, please don't," you rolled your eyes.

Slowly you sat up, you were completely disheveled: bra undone, skirt bunched awkwardly around your thighs, dress half open. He leaned forward, beckoning you closer with the crook of his finger.

"Come here and let me put you back together, doll. You're currently breaking about fifty dress code rules. You don't want me to report you to Penguin, do you?" he teased, and you snorted, but scooched forward, shaking your head with a soft giggle.

"You're one to talk, Jerome, with your cock hanging out of your trousers," you jested.

Ignoring your remark, he stood and hooked your bra back together before he began buttoning your dress. He felt your fingers tugging at his belt silently asking him to come closer, and he did with a grin. Working quietly, you tucked him back together, before buckling and zipping him up. He was just about to ask you to stand so he could fix your skirt when he noticed one of your shoes had fallen off. Spying its shining black sole a few feet behind a chair, he grinned.

"Allow me, m'lady," he said, winking as he went to retrieve it.

Kneeling in front of you still perched on his desk, he gently slid the errant shoe back onto your foot, his fingers teasing at the back of your ankle as he did so. He smiled up at you and pressed a kiss to your skin.

"If you could stand, please. I'll fix that troublesome dress of yours," he instructed.

With a grin to match his own, you hopped off the desk. He smoothed his hands up your sides, tugging your dress taut before pulling the skirt part down over it.

"There, voilà," he smirked, jerking the fabric a little to the side in order to center it. "as if nothing happened."

You parted ways soon after that, he made some cheesy promise about how he was going to be seeing you again very soon, especially after how the fun you two just had.

Shortly after his departure, you finished up your tasks back at the dining room of the club until you heard your boss, Oswald, screaming to the top of his lungs in the room you and Jerome had just fucked in. You rushed over to peek from behind the door to see him next to Butch, throwing a fit.

"Why the fuck does it smell like sex in here?!" he barked, nearly ripping his hair out of his head. "I am going to personally kill the two people who fucked on my property, I don't care who they are!" he yelled, making you almost flinch from surprise. You listened for a little while longer and when Butch spoke up, you heard your name mentioned in a whisper and that's when you scampered off.


End file.
